20. Bill Laimbeer

Sport: Basketball
Year of the Mask: 1990
Unless you were a fan of the Bad Boys Pistons of the '80s, Bill Laimbeer was most likely the type of player you loved to loathe. His repulsive attitude on the hardwood often led to fights and injuries such as the broken eye socket suffered in 1990 which required this mask. The only thing more annoying than Bill Laimbeer was Bill Laimbeer in a ridiculous mask.